Spectinomycin is a known antibiotic and was first prepared by a microbiological process, see U.S. Pat. No. 3,234,092. Since that time spectinomycin has been synthesized chemically, see J. Am Chem. Soc. 101, 19 (1979) and U.S. Pat. No. 4,351,771.
6'-Methylspectinomycin analogs and intermediates useful in production of 6'-methylspectinomycin are known, see U.S. Pat. Nos. 4,380,651 and 4,380,652.
U.S. Pat. No. 4,465,848 discloses a process for demethylation of spectinomycin and its analogs and realkylation of the intermediates. U.S. Pat. No. 4,532,336 discloses 6'-alkylspectinomycins and intermediates useful in preparation thereof.
U.S. Pat. No. 4,351,771 claims 6'-alkenylspectinomycins.
The present invention involves 6'-thiomethyl-substituted spectinomycins (XII) pharmacologically active end products and intermediates enamine (V), 6'-methylidene substituted spectinomycins (VI), triprotected 6'-alkenyl-4',5'-didehydrospectinomycins (VII), amine protected 6'-alkenylspectinomycins (VIII), triprotected 6'-thiomethyl-substituted spectinomycins (X) and amine protected 6'-thiomethyl-substituted spectinomycins (XI) intermediates.